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Sigma-Aldrich

CP-55940

>98% (HPLC), powder

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Synonym(s):
5-(1,1-Dimethylheptyl)-2-[5-hydroxy-2-(3-hydroxypropyl)cyclohexyl]phenol
Empirical Formula (Hill Notation):
C24H40O3
CAS Number:
83002-04-4
Molecular Weight:
376.57
MDL number:
MFCD00673965
UNSPSC Code:
12352200
PubChem Substance ID:
24278295
NACRES:
NA.77

Quality Level

100

Assay

>98% (HPLC)

form

powder

optical activity

[α]/D -24 to -30°, c = 0.2 in chloroform-d

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated

solubility

DMSO: 15 mg/mL
H2O: slightly soluble

storage temp.

2-8°C

SMILES string

CCCCCCC(C)(C)c1ccc([C@@H]2C[C@H](O)CC[C@H]2CCCO)c(O)c1

InChI

1S/C24H40O3/c1-4-5-6-7-14-24(2,3)19-11-13-21(23(27)16-19)22-17-20(26)12-10-18(22)9-8-15-25/h11,13,16,18,20,22,25-27H,4-10,12,14-15,17H2,1-3H3/t18-,20-,22-/m1/s1

InChI key

YNZFFALZMRAPHQ-SYYKKAFVSA-N

Gene Information

human ... CNR1(1268) , CNR2(1269)
rat ... Cnr1(25248)

Application

CP-55940 has been used as a cannabinoid agonists in Chinese hamster ovary (CHO) expressing cannabinoid receptor 2(CB2).

Biochem/physiol Actions

CP-55940 is a nonclassical cannabinoids (NCCs), which lack the tetrahydropyran ring. CP-55940, a derivative of CP-47,497 is enantioselective. Due to its amphipathic nature, CP-55940 tethers in biological membrane making it favourable for the cannabinoid receptor interaction. CP-55940 belongs to the cyclohexylphenol category and modulates the brain lipidome leading to dysregulation especially during adolescence. It inhibits capsaicin-evoked sensitization of nociceptive and spinal dorsal horn neurons.
CP-55940 is a selective cannabinoid receptor agonist.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H336

Hazard Classifications

STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Broad and Region-Specific Impacts of the Synthetic Cannabinoid CP 55,940 in Adolescent and Adult Female Mouse Brains
Leishman E, et al.
Frontiers in Molecular Neuroscience, 11, 436-436 (2018)
The conformational properties of the highly selective cannabinoid receptor ligand CP-55,940
Xie XQ, et al.
The Journal of Biological Chemistry, 271(18), 10640-10647 (1996)
David R Maguire et al.
Psychopharmacology, 235(8), 2357-2365 (2018-06-04)
Cannabinoid receptor agonists such as delta-9-tetrahydrocannabinol (Δ9-THC) enhance the antinociceptive potency of mu opioid receptor agonists such as morphine, indicating that opioid/cannabinoid mixtures might be effective for treating pain. However, such enhancement will be beneficial only if cannabinoids do not
Pradeep Paudel et al.
Marine drugs, 19(6) (2021-07-03)
Phlorotannins are polyphenolic compounds in marine alga, especially the brown algae. Among numerous phlorotannins, dieckol and phlorofucofuroeckol-A (PFF-A) are the major ones and despite a wider biological activity profile, knowledge of the G protein-coupled receptor (GPCR) targets of these phlorotannins
Cannabinoid agonist, CP 55,940, prevents capsaicin-induced sensitization of spinal cord dorsal horn neurons
Johanek LM and Simone DA
Journal of Neurophysiology, 93(2), 989-997 (2005)
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Synthetic Cannabinoid Analysis

A large variety of cannabinoid drug standards, along with an HPLC method with the Supelco Ascentis® Express RP-Amide column, are presented in this article.

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